Options Boot Camp 375: 0dte Options and the Dangers of Contra-Exercise

This episode of Options Boot Camp dives into one of the most significant shifts in the equity markets: the arrival of 0DTE (Zero Days to Expiration) options for single stocks like Nvidia, Tesla, and Apple. While the excitement is high, hosts Mark Longo and Dan Passarelli highlight a critical technical risk that many retail traders overlook—Contra-Exercise. Episode Summary The "0DTE era" has officially expanded beyond cash-settled indices like the SPX. With single-name equity options now listing for Mondays, Wednesdays, and Fridays, traders face a new logistical hurdle: physical settlement. Unlike cash-settled indices, equity options result in the delivery of actual stock, making the after-hours window a potential minefield for "pin risk" and unexpected assignments. Key Discussion Points: The 0DTE Expansion: Why names like IBIT, NVDA, and TSLA are joining the zero-day fray and what it means for market volatility. Understanding Contra-Exercise: The mechanics of the "Do Not Exercise" (DNE) order and how to force the exercise of out-of-the-money options. The After-Hours Window: Why the 4:00 PM ET close isn't the end of your risk, and how news after the bell can trigger "ghost" assignments. Broker Deadlines: A breakdown of how different brokers handle the cutoff times for contra-instructions. Risk Management: Why the "best case scenario" is almost always closing your position before the closing bell. Go to tastytrade.com/podcasts and see why Investopedia named tastytrade the best broker for options in 2024. Genius loves company.

In this episode, Mark Longo and Dan Passarelli take a nostalgic trip back to the 80s to become the Masters of the Volatility Universe. Whether you're a "Prince Adam" of the markets or just starting your basic training, this episode is a comprehensive refresher on the most important force in options pricing: Volatility. The Drill Instructors break down: Volatility as the Speedometer: Why direction matters less than velocity when measuring vol. Realized vs. Historical Volatility: Understanding the concrete, backward-looking data of price swings. Implied Volatility (IV): Why Mark calls it the "Fudge Factor" of the options market and how it acts as a forward-looking forecast. The Volatility Risk Premium (VRP): Why options are often "overpriced" and how premium sellers harvest that edge. Supply and Demand: Dan's take on why IV is often more about market noise than actual future predictions. 2026 VIX Prognostications: Where will the "Fear Gauge" end the year? Dan puts his official number on the record.

Options Boot Camp Episode 373 explores two major themes shaping today's options market: the rapid rise of IBIT options volume and the most misunderstood options trading strategies. Hosts Mark Longo and Dan Passarelli break down why strategies like cash-secured puts, long puts, straddles, butterflies, and iron condors are frequently misused by traders, often due to poor education and unrealistic expectations. The discussion explains why "being okay with assignment" is not the same as wanting assignment, and how that distinction can dramatically change trading outcomes. The episode also examines how IBIT options rivaling VIX in volume has reshaped Bitcoin options trading, altered volatility skew, and attracted institutional and premium-selling participants to crypto markets. Designed for traders of all experience levels, Options Boot Camp delivers practical options education, real-world examples, and clear explanations of complex strategies. Produced by the Options Insider Radio Network.

Kick off the new year with a fresh set of options trading resolutions on this episode of Options Boot Camp. Hosts Mark Longo and Dan Passarelli dive into what traders should be focusing on in 2026 — from expanding your options strategy toolbox to managing risk, sizing trades properly, and knowing when not to trade at all. With many traders coming off years of strong equity performance, the hosts explore whether it's time to rethink long-only strategies, reduce concentration risk, or introduce new approaches like stock substitution, LEAPS, downside hedging with puts, and portfolio diversification through options strategies. The conversation also covers why relying on a single options strategy can be dangerous, how to diversify your Greeks, and what newer traders often overlook when markets change. This episode also looks ahead to potential options market trends in 2026, including zero-DTE options, 24-hour trading, prediction markets, crypto volatility, and global market opportunities. Along the way, Mark and Dan reference past Options Boot Camp episodes to help listeners build a deeper understanding of puts, volatility, and long-term strategy planning.

What a year it was for the options market! From the "unprecedented" volatility of April to a record-breaking 15 billion contracts traded, 2025 was anything but boring. In this special year-end extravaganza, your drill instructors Mark Longo and Dan Passarelli (Market Taker Mentoring) look back at the Top 10 Episodes of 2025 to see what resonated most with traders during this historic year. Mark and Dan dive into the data to reveal the most downloaded topics of the year, spanning everything from high-intensity hedging strategies to the surprising winner of the #1 spot. Whether you are a veteran of "Liberation Day" or a newcomer looking to get into peak options trading shape, this countdown is the ultimate refresher on the strategies that defined the market this year. In this episode, the "Dynamic Duo" discusses: The Top 10 Countdown: Which episodes took the crown? (Hint: Leaps and Covered Calls were heavy hitters). Volatility Redefined: Revisiting the historic spikes of April and the role of inverse volatility products like SVXY. Retail Power: How the 15-billion-contract milestone changed the landscape for retail traders. Strategy Deep Dives: Reflections on Gamma Scalping, Iron Condors, and the enduring popularity of "The Poor Man's Covered Call." The VIX Average: Dan breaks down the long-term average of the VIX and how anomalies skew the data. Holiday Fun: The definitive (and divisive) ranking of the best Christmas movies. Support for this Episode Special thanks to Tastytrade—named the best broker for options in 2024 by Investopedia. See why at tastytrade.com/podcasts .

In this episode of Options Boot Camp, your drill instructors Mark Longo and Dan Passarelli dive back into the trenches to tackle a recurring nightmare for retail traders: why "perfect" vertical spreads sometimes result in losses. Following up on a "horror story" from a previous episode involving Marvell (MRV), the team breaks down the mechanics of spread books, broker liquidations, and the hidden risks of trading around major events. In This Episode, You'll Learn: The Marvell Meltdown: A deep dive into a listener's trade where a winning call vertical on MRV resulted in a loss due to after-hours volatility and broker liquidation. The Reality of Vertical Spreads: Why the P&L diagram is only half the story. We discuss why vertical spreads often perform worse than expected prior to expiration and the role theta plays in the final payoff. Legging vs. Spread Orders: When should you attempt to "leg out" of a spread? Dan and Mark discuss the risks of delta exposure when breaking apart a vertical in a fast-moving market. Broker Routing & PFOF: How Payment for Order Flow and specific broker "spread books" (like Robinhood's) can impact your execution quality, especially in illiquid names. Market Maker Psychology: What determines the width of a bid-ask spread? Dan explains how volatility risk and liquidity determine the "toll" you pay to enter and exit a trade. Mail Call: The team answers listener questions about avoiding spreads during earnings and the rise of prediction markets (binary betting). Chapters & Key Moments: 00:00 – Introduction and The Quintuple Content Palooza 03:15 – Follow-up: The Marvell Vertical Spread Disaster 07:45 – The pros and cons of "Legging" out of a trade 12:20 – Tips for dealing with unresponsive brokers during liquidations 16:30 – Market Taker Question: What drives the Bid-Ask Spread? 21:10 – Prediction Markets: Is it a trade or a bet? 25:40 – Silver and Crypto: The Question of the Week Special thanks to our sponsor: TastyTrade.com/podcasts

In this episode of Options Boot Camp, hosts Mark Longo and Dan Passarelli (Market Taker Mentoring) dive deep into the mechanics of the Wheel Strategy—one of the most popular frameworks for generating consistent options income. Whether you are selling cash-secured puts or managing covered calls, the "Wheel" is a powerful tool for any trader's playbook, but what happens when the market moves against you? Mark and Dan break down the specific scenarios traders face when a trade goes south, offering a masterclass in position management and cost basis reduction. Key Topics Covered in This Episode: Managing Losing Trades: What to do when your initial put sale goes in-the-money. Stock Repair Strategies: How to use the "Repair Manual" to recover from underwater positions without adding more capital. Averaging Down vs. Rolling: The pros and cons of lowering your entry price in a declining market. The Importance of Objectives: Why a clear "exit plan" is the most critical part of the Wheel Strategy. Advanced Covered Calls: Strategic strikes for when you've been assigned the underlying stock.

In this vital Options Bootcamp episode, host Mark Longo from The Options Insider provides an in-depth tutorial on butterfly spread strategies alongside guest Brian Overby from OptionsPlaybook.com. They explore both traditional and advanced butterfly strategies—including the Open Wing Butterfly (often known as a Broken Wing Butterfly) and the Intrinsic Value Butterfly—explaining their practical options trading applications and defined risk/reward benefits. This is essential options trading education for neutral, low-volatility markets. Additionally, they address a listener's puzzling options scenario involving Marvell ($MRVL) stock and offer clear resolution strategies for similar trading challenges, emphasizing proper broker interaction and order management.

In this episode of Options Boot Camp, hosted by Mark Longo (The Options Insider) and Dan Passarelli (Market Taker Mentoring), the discussion covers a variety of topics ranging from the importance of implied volatility and the concept of IV crush, to the future of premium selling in zero-day options, and the growing trend of prediction markets. The hosts also tackle listener questions about trading strategies and market behavior, debate the classification of cranberry sauce as a side dish or topping, and share humorous anecdotes.

This episode of Options Boot Camp delves deeply into various aspects of binary options trading. The hosts discuss the pros and cons of different types of binary contracts, including $1 to $100 and penny to $1 variations, and explore complications like last-minute fluctuations and liquidity issues. Listeners' questions are addressed, covering topics such as arbitrage opportunities for retail traders and the differences between single-strike and multi-strike binaries. The show also highlights the importance of exiting positions before expiration to avoid unpredictable last-minute price swings.  HOST: Mark Longo, The Options Insider CO-HOST: Dan Passarelli, Market Taker Mentoring